1,3-CYCLOHEXADIENE Chemical Properties

Melting point:

-98 °C

Boiling point:

80 °C (lit.)

Density 

0.841 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.474(lit.)

Flash point:

−2 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to light yellow

Water Solubility 

Slightly miscible with methanol. Immiscible with water.

BRN 

506024

Dielectric constant

2.6600000000000001

Stability:

Light Sensitive

LogP

2.470

CAS DataBase Reference

592-57-4(CAS DataBase Reference)

EPA Substance Registry System

1,3-Cyclohexadiene (592-57-4)

Safety Information

Hazard Codes 

F

Risk Statements 

11-10-37

Safety Statements 

9-16-29-33

RIDADR 

UN 3295 3/PG 2

WGK Germany 

3

RTECS 

GU4702350

F 

9

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29021990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,3-CYCLOHEXADIENE Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Uses

1,3-Cyclohexadiene can undergo:
C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.
Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.
Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.
Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.

Uses

1,3-Cyclohexadiene is used as a hydrogen donor in transfer hydrogenation. It is used in the conversion to benzene. It is useful in the study of proteomics research.

Uses

1,3-Cyclohexadiene can undergo:

• C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.
• Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.
• Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.
• Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.

Definition

ChEBI: Cyclohexa-1,3-diene is a cyclohexadiene.

Preparation

1,3-Cyclohexadiene has been prepared by dehydration of cyclohexen-3-ol, by pyrolysis at 540° of the diacetate of cyclohexane-1,2-diol, by dehydrobromination with quinoline of 3-bromocyclohexene, by treating the ethyl ether of cyclohexen-3-ol with potassium bisulfate, by heating cyclohexene oxide with phthalic anhydride, by treating cyclohexane-1,2-diol with concentrated sulfuric acid, by treatment of 1,2-dibromocyclohexane with tributylamine, with sodium hydroxide in ethylene glycol, and with quinoline, and by treatment of 3,6-dibromo-cyclohexene with sodium.

Purification Methods

Distil the diene from NaBH4 or Na under N2 and collect it in a trap cooled in Dry Ice. It is highly flammable. [Marvel & Martell, J Am Chem Soc 81 450 1959, Beilstein 5 IV 382.]

1,3-CYCLOHEXADIENE(592-57-4)Related Product Information

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